Triethylamine → HCID 59971446, compound

HRID 382031Notes

Reaction equation

HRID 382031 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2/[C:11](=[CH:19]/[C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)/[C:12](=[O:18])[NH:13]3)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[C:32]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38])#[N:33]>C(Cl)(Cl)Cl>[O:18]=[C:12]1[NH:13][C:14]2[C:10](/[C:11]/1=[CH:19]/[C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)=[C:9]([C:5]1[CH:4]=[C:3]([NH:2][C:37](=[O:38])[C:36]3[CH:40]=[CH:41][CH:42]=[C:34]([C:32]#[N:33])[CH:35]=3)[CH:8]=[CH:7][CH:6]=1)[CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 9819192HCID 9819192, compound

Product 1

HCID 59971446HCID 59971446, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (Z)-4-(3-aminophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one hydrochloride (40 mg, 0.118 mmol) (from Example 5 supra) and Et3N (33 μL , 0.237 mmol) in 3 mL of chloroform was treated with 3-cyanobenzoyl chloride (22 mg, 0.130 mmol) (Aldrich), and the resulting reaction mixture was stirred at room temperature for 15 h. The reaction mixture was concentrated in vacuo to remove chloroform. The yellow residue was suspended in distilled water, and the resulting solid was collected by suction filtration to provide pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-3-cyanobenzamide (yield: 41 mg, 81%) as a yellow solid (mp 250-251° C.).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove chloroform
  4. filtrationthe resulting solid was collected by suction filtration

Sources & evidence

ORD record
ord-c23c851625d3477482b1e74ed6b51b68
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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